Jack Dorsey’s Block is laying off 40% + of their 10,000 employees.
NEWS TO KNOW
Despite reporting record profits. The stock shot up 24%.
Jack is citing wanting to move faster and use AI internally to be more productive.
If this works well for them, this will be a company blueprint others will steal.
Just a tad scary.
📚 – Answering this tough interview question
BEST FROM LAST WEEK
📝 – My 9 before 9 and 5 after 5 method
💸 – 6 things to never say in sales
Stop Asking What to Do Next
Big mistake I see all the time on sales calls: things are going well, good conversation, the prospect seems interested, and then the rep says something like “so where do you think we should go from here?” or “what makes sense for next steps?”
Sounds reasonable, right? You’re being consultative. Collaborative. Not pushy.
Actually, you just made yourself look like you don’t know what you’re doing.
That immediately tells me the sales rep didn’t prepare for the call.
Why This Backfires
When you ask the buyer to guide the process, you’re essentially saying “I’m not sure how to move this forward.”
You’re the one who’s done this hundreds of times.
They’re doing it for the first time, or maybe the third time in their career.
Who should be leading here?
Plus, it puts them in an awkward position.
Now they have to think about your sales process on top of evaluating your solution.
Most buyers will default to something vague like “let me think about it and get back to you” because you didn’t give them a clear path.
The Better Approach: Prescriptive Recommendations
Come to every call with a point of view on what should happen next. Be specific.
Then hold that recommendation loosely and let them react.
Here’s what this sounds like in practice:
Instead of: “What do you think makes sense for next steps?”
Try: “Based on what you’ve shared about your Q1 timeline, I think it makes sense to get your head of rev ops looped in as well next week so we can walk through the pricing model together. Does Tuesday or Wednesday work better for you?”
Instead of: “Where should we go from here?”
Try: “The way this typically works best is we do a technical deep dive with your engineering lead, then bring it back to you and your VP for a business case review. We could knock out the technical piece as soon as this Thursday. Does that work for you?”
Notice what happens here. You’re giving them a clear recommendation AND giving them room to correct you.
“Does that match how you’re thinking about it?” is very different from “what do you think we should do?”
The Framework
Here’s how to structure your next step recommendations:
- Reference something they said – “Based on the budget cycle you mentioned…” or “Given that your team needs this before the end of quarter…”
- State your recommendation clearly – “My recommendation would be…” or “What typically works best is…”
- Provide specific logistics – Actual days, who should be involved, how long it will take
- Create space for feedback – “Does that line up with your process?” or “Does that make sense given your timeline?”
Real Examples
After a discovery call: “Okay, so you mentioned Sarah in operations would need to sign off on this. What I’m thinking is we set up a 30-minute call with her on Friday to walk through the implementation timeline, since that seemed to be her main concern when you floated this last month. Then we could regroup with you early next week to address any questions that came up. How does that sound?”
After a demo: “The next thing we should probably do is get you access to a sandbox environment so your team can actually play around with this. I can get that set up by tomorrow, and then let’s schedule 20 minutes next Tuesday where I can answer any questions that come up as you test it. Does that work on your end?”
After a technical evaluation: “Based on what your team validated today, I think we’re in good shape to put together a proposal. What I’d like to do is send over a draft by Wednesday, then jump on a call Thursday to walk through it together so we can adjust anything before you take it to your exec team early next week. Does that timeline match what you need?”
What If They Push Back?
Perfect.
That’s exactly what you want.
When you come with a recommendation, they’ll tell you if it doesn’t fit their process.
“Actually, I need to loop in my boss before we do anything with finance.”
Great! Now you know that.
Adjust your recommendation: “Got it. So let’s set up time with your boss first, maybe a quick 15-minute call where I can give her the overview. Then we can figure out the finance conversation from there.”
You’re still leading. You’re just incorporating their feedback into your plan.
The Mental Shift
Think of yourself less like a vendor waiting for instructions and more like a doctor with a treatment plan.
A good doctor doesn’t say “so what do you want to do about your symptoms?” They say “here’s what I recommend based on what I’m seeing, and here’s why.”
Your buyers want that same confidence.
They want someone who knows the path forward because you’ve walked dozens of other companies through this exact same process.
Come with a plan. Stay flexible. But stop asking them to do your job.
